Halopyrimidines

ABSTRACT

The invention relates to novel halogenopyrimidines, to a plurality of processes for their preparation and to their use as pesticides.

The invention relates to novel halogenopyrimidines, to a pluarity ofprocesses for their preparation and to their use as pesticides.

Certain pyrimidines having a similar substitution pattern, and theirfungicidal action, are already known (GB-A 2253624). However, theactivity of these prior-art compounds is, in particular at lowapplication rates and concentrations, not entirely satisfactory in allareas of use.

This invention, accordingly, provides the novel halogenopyrimidines ofthe general formula (I)

in which

z represents in each case substituted or unsubstituted cycloalkyl, arylor hetero-cyclyl,

Q represents oxygen or sulphur,

X represents halogen and

L¹, L², L³ and L⁴ are identical or different and independently of oneanother each represents hydrogen, halogen, cyano, nitro, in each caseoptionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinylor alkylsulphonyl.

In the definitions, the saturated or unsaturated hydrocarbon chains,such as alkyl, alkanediyl, alkenyl or alkinyl, are in each casestraight-chain or branched, including in combination with heteroatoms,such as, for example, in alkoxy, alkylthio or alkylamino. Unless statedotherwise, preference is given to hydrocarbon chains having 1 to 6carbon atoms.

Halogen generally represents fluorine, chlorine, bromine or iodine,preferably fluorine, chlorine or bromine, in particular fluorine orchlorine.

Aryl represents aromatic, mono- or polycyclic hydrocarbon rings, suchas, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferablyphenyl or naphthyl, in particular phenyl.

Heterocyclyl represents saturated or unsaturated, and also aromatic,cyclic compounds in which at least one ring member is a heteroatom, i.e.an atom different from carbon. If the ring contains a plurality ofheteroatoms, these can be identical or different. Preferred heteroatomsare oxygen, nitrogen and sulphur. If the ring contains a plurality ofoxygen atoms, these are not adjacent. If appropriate, the cycliccompounds form, together with other carbocyclic or heterocyclic,fused-on or bridged rings, a polycyclic ring system. Preference is givento mono- or bicyclic ring systems, in particular to mono- or bicyclicaromatic ring systems.

Cycloalkyl represents saturated carbocyclic cyclic compounds which, ifappropriate, form a polycyclic ring system with other carbocyclic,fused-on or bridged rings.

A polycyclic ring system can be linked to a heterocyclic ring or afused-on carbocyclic ring. The thus-described heterocyclyl can also bemono- or polysubstituted, preferably by methyl, ethyl or halogen.Preference is given to mono- or bicyclic ring systems, in particular tomono- or bicyclic aromatic ring systems.

Halogenoalkoxy represents partially or fully halogenated alkoxy. In thecase of polyhalogenated halogenoalkoxy, the halogen atoms can beidentical or different. Preferred halogen atoms are fluorine and, inparticular, chlorine. If the halogenoalkoxy carries furthersubstituents, the maximum number of halogen atoms which is possible isreduced to the remaining free valencies. Unless stated otherwise,preference is given to hydrocarbon chains having 1 to 6 carbon atoms.

Halogenoalkyl represents partially or fully halogenated alkyl. In thecase of polyhalogenated halogenoalkyl, the halogen atoms can beidentical or different. Preferred halogen atoms are fluorine andchlorine, in particular fluorine. If the halogenoalkyl carries othersubstituents, the maximum possible number of halogen atoms is reduced tothe remaining free valencies. Unless stated otherwise, preference isgiven to hydrocarbon chains having 1 to 6 carbon atoms.

Furthermore, it has been found that the novel halogenopyrimidines of thegeneral formula (I) are obtained when

a) 2-(2-hydroxy-phenyl)-2-methoxyiminoacetates of the formula (II)

 in which

L¹, L², L³ and L⁴ are each as defined above

are reacted with a substituted halogenopyrimidine of the general formula(III)

 in which

Z, Q and X are each as defined above and

Y¹ represents halogen,

if appropriate in the presence of a diluent, if appropriate in thepresence of an acid acceptor and if appropriate in the presence of acatalyst, or when

b) phenoxypyrimidines of the general formula (IV)

 in which

X, L¹, L², L³ and L⁴ are each as defined above and

Y² represents halogen

are reacted with a cyclic compound of the general formula (V)

Z—Q—H  (V)

in which

Z and Q are each as defined above,

if appropriate in the presence of a diluent, if appropriate in thepresence of an acid acceptor and if appropriate in the presence of acatalyst.

Finally, it has been found that the novel halogenopyrimidines of thegeneral formula (I) have very strong activity against pests of plants.

If appropriate, the compounds according to the invention can be presentas mixtures of different possible isomeric forms, in particular ofstereoisomers, such as, for example, E and Z. What is claimed are boththe E and the Z isomers, and any mixtures of these isomers.

The invention preferably provides compounds of the formula (I) in which

Z represents cycloalkyl having 3 to 7 carbon atoms which is in each caseoptionally mono- or disubstituted by halogen, alkyl or hydroxyl;

represents heterocyclyl having 3 to 7 ring members which is optionallysubstituted by alkyl having 1 to 4 carbon atoms or halogen;

or represents phenyl or naphthyl, each of which is optionally mono- totetrasubstituted by identical or different substituents, where thepossible substituents are preferably selected from the list below:

halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl,thio-carbamoyl;

in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl,alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio,mercaptoalkyl, alkyl-sulphinyl or alkylsulphonyl having in each case 1to 8 carbon atoms;

in each case straight-chain or branched alkenyl or alkenyloxy having ineach case 2 to 6 carbon atoms;

in each case straight-chain or branched halogenoalkyl, halogenoalkoxy,halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonylhaving in each case 1 to 6 carbon atoms and 1 to 13 identical ordifferent halogen atoms;

in each case straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11identical or different halogen atoms;

in each case straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl,dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkylaminocarbonyloxy,alkenylcarbonyl or alkinylcarbonyl, having 1 to 6 carbon atoms in therespective hydrocarbon chains;

cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms; ineach case doubly attached alkylene having 3 or 4 carbon atoms,oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2carbon atoms, each of which is optionally mono- to tetrasubstituted byidentical or different substituents from the group consisting offluorine, chlorine, oxo, methyl, trifluoromethyl and ethyl;

or a grouping

 in which

A¹ represents hydrogen, hydroxyl or alkyl having 1 to 4 carbon atoms orcycloalkyl having 1 to 6 carbon atoms and

A² represents hydroxyl, amino, methylamino, phenyl, benzyl or representsin each case optionally cyano-, hydroxyl-, alkoxy-, alkylthio-,alkylamino-, dialkylamino- or phenyl-substituted alkyl or alkoxy having1 to 4 carbon atoms, or represents alkenyloxy or alkinyloxy having ineach case 2 to 4 carbon atoms,

and phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl,heterocyclyl or phenylalkyl, phenylalkyloxy, phenylalkylthio orheterocyclylalkyl having in each case 1 to 3 carbon atoms in therespective alkyl moieties and being in each case optionally mono- totrisubstituted in the ring moiety by halogen and/or straight-chain orbranched alkyl or alkoxy having 1 to 4 carbon atoms,

Q represents oxygen or sulphur,

X represents fluorine, chlorine or bromine and

L¹, L², L³ and L⁴ are identical or different and independently of oneanother each represents hydrogen, halogen, cyano, nitro, or representsalkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having ineach case 1 to 6 carbon atoms and being in each case optionallysubstituted by 1 to 5 halogen atoms.

The invention relates in particular to compounds of the formula (I) inwhich

Z represents cyclopentyl or cyclohexyl, each of which is optionallymono- or disubstituted by fluorine, chlorine, methyl, ethyl or hydroxyl;

represents thienyl, pyridyl or furyl, each of which is optionallysubstituted by methyl, ethyl or chlorine;

or represents phenyl or naphthyl, each of which is optionally mono- totetrasubstituted by identical or different substituents, where thepossible substituents are preferably selected from the list below:

fluorine, chlorine, bromine, iodine, cyano, nitro, amino, hydroxyl,formyl, carboxyl, carbamoyl, thiocarbamoyl,

methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-,3-neo-pentyl, 1-, 2-, 3-, 4-(2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-,3-, 4-, 5-(2-methylpentyl), 1-2-, 3-(3-methylpentyl), 2-ethylbutyl, 1-,3-, 4-(2,2-dimethylbutyl), 1-, 2-(2,3-dimethylbutyl), hydroxymethyl,hydroxyethyl, 3-oxobutyl, methoxymethyl, dimethoxymethyl,

methoxy, ethoxy, n- or i-propoxy, methoxymethyl, ethoxymethyl,

mercaptomethyl, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,methylthiomethyl, ethylthiomethyl,

vinyl, allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy,allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy;

trifluoromethyl, trifluoroethyl,

difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, pentafluoropropoxy, difluoromethylthio,trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinylor trifluoromethylsulphonyl,

methylamino, ethylamino, n- or i-propylamino, dimethylamino,diethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl,methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl,diethylaminocarbonyl, dimethylaminocarbonyloxy, diethylaminocarbonyloxy,benzylaminocarbonyl, acryloyl, propioloyl,

cyclopentyl, cyclohexyl,

in each case doubly attached propanediyl, ethyleneoxy, methylenedioxy,ethylenedioxy, each of which is optionally mono- to tetrasubstituted byidentical or different substituents from the group consisting offluorine, chlorine, oxo, methyl and trifluoromethyl

or a grouping

 where

A¹ represents hydrogen, methyl or hydroxyl and

A² represents hydroxyl, methoxy, ethoxy, amino, methylamino, phenyl,benzyl or hydroxyethyl, and

phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, benzyl,phenylethyl, phenylpropyl, benzyloxy, benzylthio,5,6-dihydro-1,4,2-dioxazin-3-ylmethyl, triazolylmethyl,benzoxazol-2-ylmethyl, 1,3-dioxan-2-yl, benzimidazol-2-yl, dioxol-2-yl,oxadiazolyl, 2,3-dihydro-1,4-benzodioxin-6-yl, benzodioxol-4-yl, each ofwhich is optionally mono- to tetrasubstituted in the ring moiety byhalogen and/or straight-chain or branched alkyl or alkoxy having 1 to 4carbon atoms,

Q represents oxygen,

X represents fluorine and

L¹, L², L³ and L⁴ are identical or different and independently of oneanother each represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-,s- or t-butyl.

In a preferred group of compounds of the formula (I), Z representsoptionally substituted phenyl, naphthyl or pyridyl.

In a very particularly preferred group of compounds of the formula (I),Z represents substituted phenyl, where the possible substituents arepreferably those mentioned in the preferred ranges above.

Particular preference is given to compounds of the formula (I) in whichQ represents oxygen.

Particular preference is given to compounds of the formula (I) in whichZ represents optionally substituted phenyl, where the substituents arepreferably selected from the list below: halogen, cyano, in each casestraight-chain or branched alkyl, alkylthio, alkylthioalkyl,halogenoalkyl, halogenothioalkyl.

Particular preference is given to compounds of the formula (I) in whichX is fluorine.

In a further very particularly preferred group of compounds

L¹, L² and L³ each represent hydrogen and

L⁴ represents hydrogen or represents methyl.

The abovementioned general or preferred radical definitions apply bothto the end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation.

The radical definitions given in the respective combinations orpreferred combinations of radicals specifically for these radicals are,independently of the combination given in each case, also replaced byany radical definitions of other preferred ranges.

The formula (II) provides a general definition of the2-(2-hydroxy-phenyl)-2-methoxyiminoacetates required as startingmaterials for carrying out the process a) according to the invention. Inthis formula (II), L¹, L², L³ and L⁴ each preferably or in particularhave those meanings which have already been given in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred or as being particularly preferred for L¹,L², L³ and L⁴.

The starting materials of the formula (II) are known and can be preparedby known processes (compare, for example, WO-A 94-05626, GB-A 2249092).

The formula (III) provides a general definition of thehalogenopyrimidines furthermore required as starting materials forcarrying out the process a) according to the invention. In this formula(III), Z, Q and X each preferably or in particular have those meaningswhich have already been given in connection with the description of thecompounds of the formula (I) according to the invention as beingpreferred or as being particularly preferred for Z, Q and X. Y¹represents halogen, preferably fluorine or chlorine.

The starting materials of the formula (III) are known and/or can beprepared by known methods (compare, for example, DE-A 4340181; Chem.Ber., 90 <1957> 942, 951).

The formula (IV) provides a general definition of the phenoxypyrimidinesrequired as starting materials for carrying out the process b) accordingto the invention. In this formula (IV), X, L¹, L², L³ and L⁴ eachpreferably or in particular have those meanings which have already beengiven in connection with the description of the compounds of the formula(I) according to the invention as being preferred or as beingparticularly preferred for X, L¹, L², L³ and L⁴. Y² represents halogen,preferably fluorine or chlorine.

The starting materials of the formula (IV) are novel and also form partof the subject-matter of the present application. They are importantintermediates, for example and preferably for preparing pesticides.

The phenoxypyrimidines of the general formula (IV) are obtained (Processb-1) when 2-(2-hydroxy-phenyl)-2-methoxyimino-acetates of the formula(II) are reacted with a trihalogenopyrimidine of the general formula(VI)

in which

X, Y¹ and y2 are identical or different and each represents halogen,

if appropriate in the presence of a diluent, if appropriate in thepresence of an acid acceptor and if appropriate in the presence of acatalyst.

The hydroxy compounds of the formula (II) required as starting materialsfor carrying out the process b-1) according to the invention havealready been described in connection with the description of the processa) according to the invention.

The formula (VI) provides a general definition of thetrihalogenopyrimidines furthermore required as starting materials forcarrying out the process b-1) according to the invention. In thisformula (VI), X, Y¹ and Y² each represent halogen, preferably fluorineor chlorine.

The trihalogenopyrimidines are known and/or can be prepared by knownmethods (compare, for example, Chesterfield et al., J. Chem. Soc., 1955;3478, 3480; WO-A 97-27189).

The formula (V) provides a general definition of the cyclic compoundsfurthermore required as starting materials for carrying out process b)according to the invention. In this formula (V), Z and Q each preferablyor in particular have those meanings which have already been given inconnection with the description of the compounds of the formula (I)according to the invention as being preferred or as being particularlypreferred for Z and Q.

The cyclic compounds of the formula (V) are known chemicals forsynthesis or can be prepared by simple methods.

Suitable diluents for carrying out the processes a), b) and b-1)according to the invention are all inert organic solvents. Theseinclude, by way of example and by way of preference, ethers, such as,for example, diethyl ether, diisopropyl ether, methyl t-butyl ether,methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane or anisole; nitrites, such as, for example,acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile;amides, such as, for example, N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; sulphoxides, such as, for example,dimethyl sulphoxide; or sulphones, such as, for example, sulpholane.

If appropriate, the processes a), b) and b-1) according to the inventionare carried out in the presence of a suitable acid acceptor. Suitableacid acceptors are all customary inorganic or organic bases. Theseinclude, by way of example and by way of preference, alkaline earthmetal and alkali metal hydrides, hydroxides, alkoxides, carbonates orbicarbonates, such as, for example, sodium hydride, sodium amide,potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodiumcarbonate, potassium carbonate, potassium bicarbonate and sodiumbicarbonate.

Suitable catalysts for the processes a), b) and b-1) according to theinvention are all copper(I) salts, such as, for example, copper(I)chloride, copper(I) bromide or copper(I) iodide.

When carrying out the processes a), b) and b-1) according to theinvention, the reaction temperatures can be varied within a relativelywide range. In general, the processes are carried out at temperaturesfrom −20° C. to 100° C., preferably at temperatures from −10° C. to 80°C.

For carrying out the process a) according to the invention for preparingthe compounds of the formula (I), generally 0.5 to 15 mol, preferably0.8 to 8 mol, of substituted halogenopyrimidine of the formula (III) areemployed per mole of the 2-(2-hydroxy-phenyl)-2-methoxyimino-acetate ofthe formula (II).

For carrying out the process b) according to the invention for preparingthe compounds of the formula (I), generally 0.5 to 15 mol, preferably0.8 to 8 mol, of a cyclic compound of the general formula (V) areemployed per mole of the phenoxypyrimidine of the formula (IV).

For carrying out the process b-1) according to the invention forpreparing the compounds of the formula (IV), generally 1 to 15 mol,preferably 2 to 8 mol, of a trihalogenopyrimidine of the general formula(VI) are employed per mole of the2-(2-hydroxy-phenyl)-2-methoxyimino-acetate of the formula (II).

All processes according to the invention are generally carried out underatmospheric pressure. However, it is also possible to operate underelevated or reduced pressure—in general between 0.1 bar and 10 bar.

The practice of the reaction and the work-up and isolation of thereaction products is carried out by generally customary processes(compare also the Preparation Examples).

Biology

The compounds according to the invention have potent microbicidalactivity and can be employed for controlling undesirable microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides are employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides are employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above are mentioned as examples, but not by wayof limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidia form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for exanple, Cochliobolus sativus(conidia form: Drechslera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culnorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Altemaria species, such as, for example, Altemaria brassicae; and

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of aerial parts of plants, of propagation stock and seeds, andof the soil.

According to the invention, it is possible to treat all plants and partsof plants. By plants are to be understood here all plants and plantpopulations such as desired and undesired wild plants or crop plants(including naturally occurring crop plants). Crop plants can be plantswhich can be obtained by conventional breeding and optimization methodsor by biotechnological and genetic engineering methods or combinationsof these methods, including the transgenic plants and including plantcultivars which can or cannot be protected by varietal property rights.Parts of plants are to be understood as meaning all above-ground andbelow-ground parts and organs of plants, such as shoot, leaf, flower androot, examples which may be mentioned being leaves, needles, stems,trunks, flowers, shoot-bodies, fruits and seeds and also roots, tubersand rhizomes. Parts of plants also include harvested plants andvegetative and generative propagation material, for example seedlings,tubers, rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormulti-layer coating.

The active compounds according to the invention can be employedparticularly successfully for controlling cereal diseases, such as, forexample, against Leptosphaeria species, diseases in viticulture, fruitand vegetable growing, such as, for example, against Venturia,Sphaerotheca, Phytophtora and Plasmopara species, or rice diseases, suchas for example, against Pyricularia species.

Furthermore, the active compounds according to the invention may also beemployed to increase the yield of crops. Moreover, they have reducedtoxicity and are tolerated well by plants.

If appropriate, the active compounds according to the invention can, incertain concentrations and application rates, also be used asherbicides, for influencing plant growth and for controlling animalpests. If appropriate, they can also be used as intermediates andprecursors for synthesizing other active compounds.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employfor example organic solvents as auxiliary solvents. Suitable liquidsolvents are essentially: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide or dimethyl sulphoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as highlydisperse silica, alumina and silicates. Suitable solid carriers forgranules are: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, or else syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks.Suitable emulsifiers and/or foam formers are: for example nonionic andanionic emulsifiers, such as polyoxyethylene fatty acid esters,polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycolethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or elseprotein hydrolysates. Suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, is also possible.

In addition, the compounds of the formula (I) according to the inventionalso have very good antimycotic action. They have a very broadantimycotic activity spectrum, in particular against dermatophytes andyeasts, moulds and diphasic fungi (for example against Candida speciessuch as Candida albicans, Candida glabrata), against Epidermophytonspecies, such as Epidermophyton floccosum, Aspergillus species, such asAspergillus niger and Aspergillus fumigatus, Trichophyton species, suchas Trichophyton mentagrophytes, Microsporon species, such as Microsporoncanis and audouinii. The list of these fungi constitutes by no means alimitation of the mycotic spectrum that can be covered, but only hasillustrative character.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. Application is carried out in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading, and the like. Furthermore, it is possible to applythe active compounds by the ultra-low-volume method, or to inject theactive compound preparation or the active compound itself into the soil.It is also possible to treat the plant seed.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the type of application. In the treatment of partsof plants, the application rates of active compound are generallybetween 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. In thetreatment of seed, the application rates of active compound aregenerally between 0.001 and 50 g per kilogram of seed, preferablybetween 0.01 and 10 g per kilogram of seed. In the treatment of thesoil, the application rates of active compound are generally between 0.1and 10,000 g/ha, preferably between 1 and 5000 g/ha.

The active compounds are suitable for controlling animal pests, inparticular insects, arachnids and nematodes, which are encountered inagriculture, in forestry, in the protection of stored products and ofmaterials, and in the hygiene sector, and have good plant tolerance andfavourable toxicity to warm-blooded animals. They may be preferablyemployed as crop protection agents. They are active against normallysensitive and resistant species and against all or some stages ofdevelopment. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. andSchistocerca gregaria.

From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Phthiraptera, for example, Pediculus humanuscorpons, Haematopinus spp., Linognathus spp., Trichodectes spp. andDamalinia spp.

From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi and Frankliniella accidentalis.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcomi, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psyllaspp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofinannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon soistitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp. and Liriomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus,Latrodectus mactans, Acarus siro, Argas spp., Omithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp., Brevipalpus spp.

The phytoparasitic nematodes include, for example, Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.

They can be deployed with particular success to combat plant-harminginsects, such as against, for example, the caterpillars of thediamondback moth (Plutella maculipennis).

The active compounds can be converted to the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound and microencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants, and/or foam formers.

If the extender used is water, it is also possible to employ for exampleorganic solvents as auxiliary solvents. Essentially, suitable liquidsolvents are: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols such as butanol orglycol and also their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulphoxide, and alsowater.

Suitable Solid Carriers are

for example ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as highly disperse silica,alumina and silicates; as solid carriers for granules there aresuitable: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, and also syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks;as emulsifiers and/or foam formers there are suitable: for examplenonionic and anionic emulsifiers, such as polyoxyethylene fatty acidesters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand also protein hydrolysates; as dispersants there are suitable: forexample lignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in theirformulations, can also be used as a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides, for example towiden the activity spectrum or to prevent the build-up of resistance. Inmany cases, synergistic effects are obtained, i.e. the activity of themixture is greater than the activity of the individual components.

Examples of particularly advantageous co-components are the followingcompounds:

Fungicides

aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, Rhalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furrmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB), quinoxyfen,

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclasis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

(E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

1-isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]carbonyl]-propyl}-carbamate,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,

1-(2-methyl-1-naphthalenyl)-1H-pyrrol-2,5-dione,

1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidindione,

1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

1-[[2-(4-chlotophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

2,6-dichloro-5-(methylthio)-4pyrimidinyl-thiocyanate,

2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

2-aminobutane,

2-bromo-2-(bromomethyl)-pentanedinitrile,

2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

2-phenylphenol (OPP),

3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrol-2,5-dione,

3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

8-hydroxyquinoline sulphate,

9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

bis-(1-methylethyl)-3-methyl4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,

cis-1-(4-chlorophenyl)-2-(1 H-1,2,4-triazol-1-yl)-cycloheptanol,

cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,

ethyl[(4-chlorophenyl)-azo]-cyanoacetate,

potassium bicarbonate,

methanetetrathiol-sodium salt,

methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

N-(6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

N-formyl-N-hydroxy-DL-alanine sodium salt,

O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,

Bactericides

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbarnate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides

abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,aldoxycarb, alphacypermethrin, alphamethrin, amitraz, avermectin, AZ60541, azadirachtin, azamethiphos, azinphos A, azinphos M, azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,bifenazate, bifenthrin, bioethanomethrin, biopermethrin, BPMC, bromophosA, bufencarb, buprofezin, butathiofos, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, cis-resmethrin, cispermethrin, clocythrin, cloethocarb,clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin,cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlorvos, diflubenzuron, dimethoate, dimethylvinphos,diofenolan, disulfoton, docusat-sodium, dofenapyn,

eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole,etrimfos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb,fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,furathiocarb,

granulosis viruses,

halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,

imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

nuclear polyhedrosis viruses,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, monocrotophos,

naled, nitenpyram, nithiazine, novaluron,

omethoate, oxamyl, oxydemethon M,

Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb, propoxur,prothiofos, prothoate, pymetrozine, pyraclofos, pyresmethrin, pyrethrum,pyridaben, pyridathion, pyrimidifen, pyriproxyfen,

quinalphos,

ribavirin,

salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, theta-cypermethrin, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox,thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate,triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron,trimethacarb,

vamidothion, vaniliprole, Verticillium lecanii,

YI 5302,

zeta-cypermethrin, zolaprofos,

(1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

(3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,

1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,

2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,

2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

3-methylphenyl propylcarbamate,

4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,

4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

Bacillus thuringiensis strain EG-2348,

[2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate,

[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,

N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,

N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.

It is also possible to admix other known active compounds, such asherbicides, fertilizers and growth regulators.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergistic agents. Synergistic agents are compoundswhich increase the action of the active compounds, without it beingnecessary for the synergistic agent added to be active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

When used against hygiene pests and pests of stored products, the activecompound is distinguished by an excellent residual action on wood andclay as well as a good stability to alkali on limed substrates.

The preparation and the use of the active compounds according to theinvention is demonstrated by the examples below.

The examples below serve to illustrate the invention. However, theinvention is not limited to the examples.

Preparation Examples Example 1

Methyl2-{2-[6-(3-fluorophenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}-2-methoxyiminoacetate

Process a)

With cooling, 4 g (0.0287 mol) of potassium carbonate are added to amixture of 4.6 g (0.0221 mol) of methyl2-(2-hydroxyphenyl)-2-methoxyiminoacetate and 5 g (0.0221 mol) of4-(3-fluorophenoxy)-5,6-difluoropyrimidine in 50 ml of acetonitrile, andthe mixture is stirred at 25° C. for 12 hours. The reaction mixture ispoured into 400 ml of water and extracted three times with in each case150 ml of ethyl acetate, the organic phase is dried over sodium sulphateand the solvent is distilled off under reduced pressure. The residue isstirred with diisopropyl ether and the resulting solid is filtered offand dried. This gives 7.3 g (79.5% of theory) of methyl2-{2-[6-(3-fluorophenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}-2-methoxyiminoacetate.

HPLC: logP=3.46

The compounds of the formula (I-a) mentioned in Table 1 below areobtained analogously to Example 1, and in accordance with thespecifications given in the general description of the process.

TABLE 1 (I-a)

Ex. No. Q X Z logP*  2 O F 2-chlorophenyl 3.6  3 O F 2,4-dimethylphenyl3.99  4 O F 2-fluorophenyl 3.40  5 O F 2,5-dimethylphenyl 3.97  6 O F2-difluoromethoxyphenyl 3.54  7 O F 2,3-dimethylphenyl 3.88  8 O F2,3-dichlorophenyl 4.05  9 O F phenyl 3.33 10 O F 2,5-dichlorophenyl4.12 11 O F 3-chloro-2-methylphenyl 4.12 12 O F 2-cyanophenyl 3.07 13 OF 2-bromophenyl 3.66 14 O F 2-ethylthiophenyl 3.86 15 O F 2-propylphenyl4.26 16 O F 2-ethylthiomethylphenyl 3.97 17 O F 2-methylphenyl 3.62 18 OF 3-trifluoromethylphenyl 4.04 19 O F 3-bromophenyl 3.96 20 O F3-cyanophenyl 3.23 21 O F 2,3-dimethoxyphenyl 3.40 22 O F2-isopropoxyphenyl 3.89 23 O F 2-iodophenyl 3.84 24 O F2-nitro-3-methylphenyl 3.60 25 O F 3-dimethylaminophenyl 3.57 26 O F2-methyl-3-nitrophenyl 3.62 27 O F 2,4-difluorophenyl 3.62 28 O F3,4-difluorophenyl 3.67 29 O F 4-cyanophenyl 3.19 30 O F 2-methoxyphenyl3.37 31 O F 3-methoxyphenyl 3.47 32 O F 2-ethylphenyl 4.02 33 O F2-ethoxyphenyl 3.67 34 O F 3-tert-butylphenyl 4.65 35 O F4-trifluoromethoxyphenyl 4.18 36 O F 2-methyl-4- 4.43trifluoromethoxyphenyl 37 O F 2-methoxy-4-trifluoro- 4.18 methoxyphenyl38 O F 4-trifluoromethylthiophenyl 4.45 39 O F 6-chloro-pyrid-2-yl 3.2540 O F 6-methyl-pyrid-2-yl 2.95 41 O F 6-methyl-pyrid-3-yl 2.37 42 O F2-chloro-4-trifluoromethylphenyl 4.41 43 O F 2-nitro-3-chlorophenyl 3.7144 O F 2-(2-methyl-allyl)phenyl 4.04 45 O F 3-ethylphenyl 4.12 46 O F2-(1,1,2,3,3-penta- 4.14 fluoropropoxy)phenyl 47 O F3-trifluoromethoxyphenyl 4.18 48 O F 2-benzylthiophenyl 4.43 49 O F2-chloro-4- 4.51 trifluoromethoxyphenyl 50 O F 2-chloro-4-methoxyphenyl3.77 51 O F 2-chloro-5-methoxyphenyl 4.04 52 O F 3-chloro-5-methylphenyl4.27 53 O F 3-methyl-4-methylthiophenyl 4.14 54 O F4-bromo-2-methylphenyl 4.29 55 O F 2-allyl-6-chlorophenyl 4.35 56 O F2,3,5,6-tetrafluorophenyl 3.94 57 O F 4-methylthiophenyl 3.81 58 O F5-chloro-2-methylphenyl 4.18 59 O F 3,5-dimethylphenyl 4.10 60 O F2,6-dibromophenyl 4.12 61 O F 2-allyl-5-methylphenyl 4.35 62 O F4-chloro-3-methylphenyl 4.27 63 O F 2-chloro-4-methylphenyl 4.06 64 O F3,4-dichlorophenyl 4.33 65 O F 2-naphthyl 4.00 66 O F 2-allyloxyphenyl3.69 67 O F 2-tert-butylphenyl 4.47 68 O F 3-chloro-2-cyanophenyl 69 O F2-trifluoromethylphenyl 70 O F 2-trifluoromethoxyphenyl 71 O F2-nitrophenyl 72 O F 2-mercaptomethylphenyl 73 O F 3-(phenoxy)phenyl 74O F 3-methylphenyl 75 O F 3-nitrophenyl 76 O F 3-methyliminomethylphenyl77 O F 2-fluoro-3-trifluoromethylphenyl 78 O F 3-pyridyl 79 O F4-fluorophenyl 80 O F 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl 81 O F 3,4-dimethoxyphenyl 82 O F2-chloro-4-fluorophenyl 83 O F 2-chloro-3-trifluoromethylphenyl 84 O F2,3-difluorophenyl 85 O F 2-cyano-6-methoxyphenyl 86 O F2-cyano-3-methoxyphenyl 87 O F 5-chloro-2-cyanophenyl 88 O F6-bromo-2-cyanophenyl 89 O F 2-cyano-3-fluorophenyl 90 O F4-chloro-2-cyanophenyl 91 O F 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-5-yl 92 O F 2,2-difluoro-1,3-benzodioxol-4-yl 93 O F2-ethoxymethylphenyl 94 O F 2-methoxymethylphenyl 95 O F2-chloro-3-formylphenyl 96 O F 2-cyano-3-methylphenyl 97 O F2-cyano-3-trifluoromethoxyphenyl 98 O F 2-cyano-3-difluoromethoxyphenyl99 O F 3-cyano-2-methylphenyl 100  O F 3-chloro-2-trifluoromethoxyphenyl 101  O F 3-fluoro-2-trifluoromethoxyphenyl 102  OF 2-difluoromethoxy-3-chlorophenyl 103  O F 2-difluoromethoxy-3-fluoro-phenyl 104  O F 3-chloro-2-methoxyphenyl 105  O F2-methoxy-3-methylphenyl 106  O F 2-propoxyphenyl *The logP weredetermined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC(gradient method, acetonitrile/0.1% aqueous phosphoric acid)

Preparation of a Starting Material of the Formula (III) Example (III-1)

5,6-Difluoro-(3-fluorophenoxy)-pyrimidine

11.38 g (0.085 mol) of trifluoropyrimidine are dissolved in 240 ml ofacetonitrile and admixed with 15.26 g (0.11 mol) of potassium carbonate,and the mixture is cooled to 10° C. Under argon, a solution of 9.52 g(0.085 mol) of 3-fluorophenol in 80 ml of acetonitrile is addeddropwise. The mixture is then stirred under argon, without furthercooling, for another 18 hours. The mixture is poured into 1 litre ofwater and extracted three times with in each case 150 ml of ethylacetate, and the organic phase is dried over sodium sulphate andconcentrated under reduced pressure. The residue is subjected tokugelrohr distillation. This gives 15.2 g (79.1% of theory) of5,6-difluoro-(3-fluorophenoxy)-pyrimidine of boiling point 95° C. at 0.5mbar.

Use Examples Example A Leptosphaeria Nodorum Test (Wheat)/Protective

Solvent:  25 parts by weight of N,N-dimethylacetamide Emulsifier: 0.6part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are sprayed with a sporesuspension of Leptosphaeria nodorum. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours.

The plants are placed in a greenhouse at a temperature of about 15° C.and a relative atmospheric humidity of 80%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention listed inExamples (6), (8) and (17) exhibit, at an application rate of 250 g/ha,an efficacy of 95% or more.

Example B Phytophthora Test (Tomato)/Protective

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier:  1.0 part by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Phytophthora infestans. The plants are then placedin an incubation cabin at about 20° C. and 100% relative atmospherichumidity.

Evaluation is carried out 3 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention listed inExamples (3), (4), (7), (11) and (17) exhibit, at an application rate of100 g/ha, an efficacy of 90% or more.

Example C Plasmopara Test (Grapevine)/Protective

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier:  1.0 part by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Plasmopara viticola and then remain in an incubationcabin at about 20° C. and 100% relative atmospheric humidity for 1 day.The plants are then placed in a greenhouse at about 21° C. and about 90%relative atmospheric humidity for 5 days. The plants are then moistenedand placed in an incubation cabin for 1 day.

Evaluation is carried out 6 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention listed inExamples (4), (7), (11) and (17) exhibit, at an application rate of 100g/ha, an efficacy of 95% or more.

Example D Venturia Test (Apple)/Protective

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier:  1.0 part by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousconidia suspension of the causative organism of apple scab Venturiainaequalis and then remain in an incubation cabin at about 20° C. and100% relative atmospheric humidity for 1 day.

The plants are then placed in a greenhouse at about 21° C. and arelative atmospheric humidity of about 90%.

Evaluation is carried out 12 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention listed inExamples (3), (4), (7), (11) and (17) exhibit, at an application rate of10 g/ha, an efficacy of 90% or more.

Example E Pyricularia Test (Rice)/Protective

Solvent:  25 parts by weight of N,N-dimethylacetamide Emulsifier: 0.6part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young rice plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Pyricularia oryzae and then remain at 100% relativeatmospheric humidity and 26° C. for 24 h. The plants are then placed ina greenhouse at 80% relative atmospheric humidity and a temperature of26° C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention listed inExamples (4), (6), (7), (8), (11) and (17) exhibit, at an applicationrate of 125 g/ha, an efficacy of 90% or more.

Example F Sphaerotheca Test (Cucumber)/Protective

Solvent:   50 parts by weight of N,N-dimethylformamide Emulsifier: 1.17parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent, and theconcentrate is diluted with water and the stated amount of emulsifier tothe desired concentration.

To test for protective activity, young cucumber plants are sprayed withthe preparation of active compound at the stated application rate. 1 dayafter the treatment, the plants are inoculated with an aqueous sporesuspension of Sphaerotheca fuliginea. The plants are then placed in agreenhouse at a relative atmospheric humidity of 70% and a temperatureof 23° C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention listed inExamples (4), (5), (7), (8), (9), (11) and (17) exhibit, at anapplication rate of 750 g/ha, an efficacy of 90% or more.

Example G Plutella Test/Synthetic Feed

Solvent:  100 parts by weight of acetone Emulsifier: 1900 parts byweight of methanol

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, and theconcentrate is diluted with methanol to the desired concentration.

A stated amount of the preparation of active compound of the desiredconcentration is pipetted onto a standardized amount of synthetic feed.After the methanol has evaporated, a film box lid covered with about 100Plutella eggs is placed onto each cavity. The freshly hatched larvaemigrate onto the treated synthetic feed.

After the desired period of time, the kill in % is determined. 100%means that all animals have been killed; 0% means that none of theanimals have been killed.

In this test, for example, the following compound of the PreparationExamples exhibits good activity: (10).

What is claimed is:
 1. A halogenopyrimidine of the formula (I)

wherein Z represents (i) cycloalkyl having 3 to 7 carbon atoms that isoptionally mono- or disubstituted by halogen, alkyl or hydroxyl; (ii)heterocyclyl selected from the group consisting of thienyl, pyridyl, andfuryl, each of which is optionally substituted by alkyl having 1 to 4carbon atoms or halogen; or (iii) phenyl or naphthyl, each of which isoptionally mono- to tetra-substituted by identical or differentsubstituents, where the substituents are selected from the groupconsisting of halogen; cyano; nitro; amino; hydroxyl; formyl; carboxyl;carbamoyl; thiocarbamoyl; straight-chain or branched alkyl,hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl,dialkoxyalkyl, alkylthio, mercaptoalkyl, alkylsulphinyl, oralkylsulphonyl having in each case 1 to 8 carbon atoms; straight-chainor branched alkenyl or alkenyloxy having in each case 2 to 6 carbonatoms; straight-chain or branched halogenoalkyl, halogenoalkoxy,halogenoalkylthio, halogenoalkylsulphinyl, or halogenoalkylsulphonylhaving in each case 1 to 6 carbon atoms and 1 to 13 identical ordifferent halogen atoms; straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11identical or different halogen atoms; straight-chain or branchedalkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy,alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl,arylalkylaminocarbonyl, dialkylaminocarbonyloxy, alkenylcarbonyl, oralkynylcarbonyl, having 1 to 6 carbon atoms in the respectivehydrocarbon chains; cycloalkyl or cycloalkyloxy having in each case 3 to6 carbon atoms; doubly attached alkylene having 3 or 4 carbon atoms,oxyalkylene having 2 or 3 carbon atoms, or dioxyalkylene having 1 or 2carbon atoms, each of which is optionally mono- to tetrasubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, oxo, methyl, trifluoromethyl, and ethyl; agrouping

 in which A¹ represents hydrogen, hydroxyl, alkyl having 1 to 4 carbonatoms, or cycloalkyl having 1 to 6 carbon atoms, and A² representshydroxyl; amino; methylamino; phenyl; benzyl; optionally cyano-,hydroxyl-, alkoxy-, alkylthio-, alkylamino-, dialkylamino-, orphenyl-substituted alkyl or alkoxy having 1 to 4 carbon atoms; oralkenyloxy or alkynyloxy having in each case 2 to 4 carbon atoms;phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl,1,3-dioxan-2-yl, benzimidazol-2-yl, dioxol-2-yl, oxadiazolyl,2,3-dihydro-1,4-benzodioxin-6-yl, or benzo-dioxol4-yl, wherein each ringmoiety is optionally mono- to trisubstituted by halogen and/orstraight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms;and phenylalkyl, phenylalkyloxy, phenylalkylthio,5,6-dihydro-1,4,2-dioxazin-3-ylmethyl, triazolylmethyl, orbenzoxazol-2-ylmethyl, wherein the respective alkyl moieties have 1 to 3carbon atoms and each ring moiety is optionally mono- to trisubstitutedby halogen and/or straight-chain or branched alkyl or alkoxy having 1 to4 carbon atoms; Q represents oxygen or sulphur; X represents fluorine,chlorine or bromine; and L¹, L², L³, and L⁴ are identical or differentand independently of one another each represents hydrogen; halogen;cyano; nitro; or alkyl, alkoxy, alkylthio, alkylsulphinyl, oralkylsulphonyl having in each case 1 to 6 carbon atoms and being in eachcase optionally substituted by 1 to 5 halogen atoms.
 2. Ahalogenopyrimidine of the formula (I) according to claim 1 wherein Zrepresents (i) cyclopentyl or cyclohexyl, each of which is optionallymono- or disubstituted by fluorine, chlorine, methyl, ethyl, orhydroxyl; (ii) thienyl, pyridyl, or furyl, each of which is optionallysubstituted by methyl, ethyl or chlorine; or (iii) phenyl or naphthyl,each of which is optionally mono- to tetra-substituted by identical ordifferent substituents, where the substituents are selected from thegroup consisting of fluorine; chlorine; bromine; iodine; cyano; nitro;amino; hydroxyl; formyl; carboxyl; carbamoyl; thiocarbamoyl; methyl;ethyl; n- or i-propyl; n-, i-, s-, or t-butyl; 1-, 2-, or 3-neo-pentyl;1-, 2-, 3-, or 4-(2-methylbutyl); 1-, 2-, or 3-hexyl; 1-, 2-, 3-, 4-, or5-(2-methylpentyl); 1-, 2-, or 3-(3-methylpentyl); 2-ethylbutyl; 1-, 3-,or 4-(2,2-dimethylbutyl); 1- or 2-(2,3-dimethylbutyl); hydroxymethyl;hydroxyethyl; 3-oxobutyl; methoxymethyl; dimethoxymethyl; methoxy;ethoxy; n- or i-propoxy; methoxymethyl; ethoxymethyl; mercaptomethyl;methylthio; ethylthio; n- or i-propylthio; methylsulphinyl;ethylsulphinyl; methylsulphonyl; ethylsulphonyl; methylthiomethyl;ethylthiomethyl; vinyl; allyl; 2-methylallyl; propen-1-yl; crotonyl;propargyl; vinyloxy; allyloxy; 2-methylallyloxy; propen-1-yloxy;crotonyloxy; propargyloxy; trifluoromethyl; trifluoroethyl;difluoromethoxy; trifluoromethoxy; difluorochloromethoxy;trifluoroethoxy; difluoromethylthio; trifluoromethylth io; d ifluorochloromethylthio; trifluoromethylsulphinyl; trifluoromethylsulphonyl;methylamino; ethylamino; n- or i-propylamino; dimethylamino;diethylamino; acetyl; propionyl; methoxycarbonyl; ethoxycarbonyl;methylaminocarbonyl; ethylaminocarbonyl; dimethylaminocarbonyl;diethylaminocarbonyl; dimethylaminocarbonyloxy; diethylaminocarbonyloxy;benzylaminocarbonyl; acryloyl; propioloyl; cyclopentyl; cyclohexyl;doubly attached propanediyl, ethyleneoxy, methylenedioxy, orethylenedioxy, each of which is optionally mono- to tetra-substituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, oxo, methyl, and trifluoromethyl; a grouping

 where A¹ represents hydrogen, methyl, or hydroxyl, and A² representshydroxyl, methoxy, ethoxy, amino, methylamino, phenyl, benzyl, orhydroxyethyl; and phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl,cinnamoyl, benzyl, phenylethyl, phenylpropyl, benzyloxy, benzylthio,5,6-dihydro-1,4,2-d ioxazin-3-ylmethyl, triazolylmethyl,benzoxazol-2-ylmethyl, 1,3-dioxan-2-yl, benzimidazol-2-yl, dioxol-2-yl,or oxadiazolyl, each of which is optionally mono- to tetrasubstituted inthe ring moiety by halogen and/or straight-chain or branched alkyl oralkoxy having 1 to 4 carbon atoms; Q represents oxygen; X representsfluorine; and L¹, L², L³, and L⁴ are identical or different andindependently of one another each represents hydrogen, methyl, ethyl, n-or i-propyl, or n-, i-, s-, or t-butyl.
 3. A halogenopyrimidine of theformula (I) according to claim 1 in which Q represents oxygen.
 4. Ahalogenopyrimidine of the formula (IV)

in which X, L¹, L², L³, and L⁴are each as defined for formula (I) inclaim 1, and Y² represents halogen.
 5. A herbicidal compositioncomprising one or more compound of claim 1, and a member selected fromthe group consisting of extenders, carriers, surfactants and mixturesthereof.
 6. A method for controlling undesirable plants comprisingapplying an effective amount of the compound of claim 1 to saidundesirable plants and/or their habitat.